2-Butyn-1-ol → HCID 22599708, compound

HRID 1759923Notes

Reaction equation

HRID 1759923 reaction equation
[H-].[Na+].[CH2:3]([OH:7])[C:4]#[C:5][CH3:6].Cl[C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[N:12]=[CH:11][N:10]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:3]([O:7][C:9]1[CH:14]=[C:13]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[N:12]=[CH:11][N:10]=1)[C:4]#[C:5][CH3:6]

Participants

6

Reactant 4

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22599692HCID 22599692, compound

Product 1

HCID 22599708HCID 22599708, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 1.5 ml of tetrahydrofuran was suspended 0.05 g of sodium hydride (60% in oil), to which 0.08 g of 2-butyn-1-ol was added, followed by stirring for 15 minutes. Then, 0.2 ml of a tetrahydrofuran solution containing 0.2 g of 4-chloro-6-(4-fluorobenzyl)pyrimidine was slowly added dropwise, followed by further stirring at room temperature for 2 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with chloroform. The chloroform layers were combined, washed with water, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.22 g of 4-(2-butynyloxy)-6-(4-fluorobenzyl)pyrimidine (the present compound (143)).

Workup

  1. additionwas slowly added dropwise
  2. stirringby further stirring at room temperature for 2 hours
  3. extractionextracted three times with chloroform
  4. washwashed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cf384f0d66684e0db35ecffd3a0b01ac
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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